Potassium Carbonate → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3-chlorophenyl)pyrimidine-2,4-diamine

HRID 2386987Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(Cl)Cl.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:20])[CH:26]=3)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product of Example 6A (69 mg, 0.246 mmol), 3-chlorophenylboronic acid (42 mg, 0.270 mmol), dichlorobis((triphenylphosphine)palladium(II) (17 mg, 0.025 mmol), and potassium carbonate (100 mg, 0.724 mmol) were combined with dioxane (5 mL) and water (1.5 mL) and heated to 100° C. overnight. The mixture was diluted with methylene chloride, washed with water, and absorbed on silica gel and purified using silica gel chromatography, eluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98 (s, 1H) 7.76-7.86 (m, 1H) 7.61 (d, J=5.76 Hz, 1H) 7.41-7.52 (m, 2H) 7.00 (s, 1H) 6.86 (s, 1H) 6.28 (s, 1H) 6.08 (s, 2H) 5.85 (s, 2H) 5.69-5.77 (m, 1H) 3.33-3.50 (m, 4H); MS (ESI+) m/z 356.9 (M+H)+.

Workup

washwashed with water
customabsorbed on silica gel
custompurified
washeluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%)

Sources & evidence

ORD record: ord-da4f9f5ed4334976a64b3289286ed8a0
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268846B2

Reaction notes

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